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100-10-7

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Identification

Name
4-Dimethylaminobenzaldehyde
CAS
100-10-7
Synonyms
4-(DIMETHYLAMINO)BENZALDEHYDE
4-(DIMETHYLAMINO)BENZENECARBONAL
4-(N,N-DIMETHYLAMINO)-BENZALDEHYDE
4-N,N-DIMETHYLBENZALDEHYDE
AKOS BBS-00003188
DIMETHYLAMINOBENZALDEHYDE
EHRICH'S REAGENT
EHRLICH ALDEHYDE REAGENT
EHRLICH ALDEHYDE REAGENT, ALCOHOLIC
EHRLICH ALDEHYDE REAGENT, WALLACE-DIAMOND
EHRLICH'S REAGENT
EHRLICH'S REAGENT SICC
EHRLICH'S SOLUTION
ERLICH'S REAGENT
HYDRAZINE METER SOLUTION
HYDRAZINE-REAGENT
n,n-dimethyl-4-amino benzaldehyde
N,N-DIMETHYL-P-AMINO BENZALDEHYDE
P-DIMETHYLAMINOBENZALDEHYDE
P-FORMYLDIMETHYLANILINE
EINECS(EC#)
202-819-0
Molecular Formula
C9H11NO
MDL Number
MFCD00003381
Molecular Weight
149.19
MOL File
100-10-7.mol

Chemical Properties

Appearance
White to off white crystalline powder
Melting point 
72-75 °C(lit.)

mp 
72-75 °C(lit.)

Boiling point 
176-177 °C (17 mmHg)
bp 
176-177 °C (17 mmHg)
density 
1.10 g/mL at 20 °C

vapor pressure 
<0.1 hPa (20 °C)
refractive index 
n20/D 1.417

Fp 
164 °C
storage temp. 
2-8°C

solubility 
alcohol: passes test (APHA ≤60)
form 
Liquid
pka
pK1:1.647(+1) (25°C)
color 
White to pale yellow
Stability:
Stable, but light sensitive. Incompatible with bases, strong oxidizing agents.
Odor
Characteristic odor
Water Solubility 
0.3 g/L (20 ºC)
Sensitive 
Air Sensitive
Merck 
14,3230
BRN 
606802
InChIKey
BGNGWHSBYQYVRX-UHFFFAOYSA-N
CAS DataBase Reference
100-10-7(CAS DataBase Reference)
NIST Chemistry Reference
Benzaldehyde, 4-(dimethylamino)-(100-10-7)
EPA Substance Registry System
100-10-7(EPA Substance)

Safety Data

Hazard Codes 
C,Xn,Xi
Risk Statements 
R36/37/38:Irritating to eyes, respiratory system and skin .
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R22:Harmful if swallowed.
R67:Vapors may cause drowsiness and dizziness.
R41:Risk of serious damage to eyes.
R37/38:Irritating to respiratory system and skin .
R10:Flammable.
R66:Repeated exposure may cause skin dryness or cracking.
R37:Irritating to the respiratory system.
R34:Causes burns.
R20:Harmful by inhalation.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
Safety Statements 
S7:Keep container tightly closed .
S16:Keep away from sources of ignition-No smoking .
S24/25:Avoid contact with skin and eyes .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S39:Wear eye/face protection .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S36:Wear suitable protective clothing .
RIDADR 
UN 2920 8/PG 2

WGK Germany 
1

RTECS 
CU5775000


8
Autoignition Temperature
445 °C
TSCA 
Yes
HS Code 
29223900
Toxicity
LD50 orally in Rabbit: > 6400 mg/kg

Raw materials And Preparation Products

Material Safety Data Sheet(MSDS)

Hazard Information

Chemical Properties
4-Dimethylaminobenzaldehyde is white to off white crystalline powder
Uses
4-(Dimethylamino)benzaldehyde is used in Ehrlich's reagent for spectrophotometric determination of hydrazine as it reacts to form azo dyes. 4-(Dimethylamino)benzaldehyde is used for determination of u rine bilirubin and porphobilinogen.
Uses
Forms colored condensation products (Schiff bases) with pyrroles1 and primary amines.2
Uses
In the presence of oxygen, some bacteria, like E. coli, are able to split tryptophan into indole and α-aminopropionic acid. This reagent is for detecting the indole and identifying the indole-positive and indole-negative microorganisms.
Uses
In the presence of oxygen, some bacteria, like E.coli, are able to split tryptophan into indole and alpha-aminopropionic acid. This reagent is for detecting the indole and identify the indole-positive and indole-negative microorganisms.
Uses
Used as derivitizing agent.
Definition
4-Dimethylaminobenzaldehyde is a mamber of the class of benzaldehydes carrying a dimethylamino substituent at position 4. Used as an indicator for detection of indoles and hydrazine.
Synthesis Reference(s)
Journal of Heterocyclic Chemistry, 26, p. 1563, 1989
Organic Syntheses, Coll. Vol. 4, p. 331, 1963
Tetrahedron Letters, 30, p. 287, 1989 DOI: 10.1016/S0040-4039(00)95181-5
General Description
Kovac′s reagent for indoles is a solution of 4-(dimethylamino)benzaldehyde and hydrochloric acid in n-butanol.

Biochem/physiol Actions
Kovac′s reagent detects the indole and aids in identifying the indole-positive and indole-negative microorganisms. E. coli can split tryptophan into indole and α-aminopropionic acid in the presence of the enzyme tryptophanase. p-Aminobenzaldehyde present in the reagent reacts with indole to form a cherry-red complex, that is soluble in alcohol, ether, and chloroform. It is recommended to use glucose free media and peptone with a high tryptophan content for the test.
Purification Methods
Crystallise DMAB from water, hexane, or from EtOH (2mL/g), after charcoal treatment, by adding excess of water. Alternatively dissolve it in aqueous acetic acid, filter, and precipitate it with ammonia. Finally recrystallise it from EtOH. It is used for the detection of pyrroles [Iyer et al. J Org Chem 59 6038 1994]. [Beilstein 14 IV 51.]

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